Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron
作者： Shiue-Shien Weng
DOI: 10.1016/J.TETLET.2009.07.077
关键词:
摘要: A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation peracetylated glycosides with various alkyl aryl mercaptans. Due to neighboring participation, anomerically pure β-thioglycosides were obtained good high yields exclusive diastereocontrol.
elsevier.com
sci-hub.se 参考文章(29)
Shaheer H. Khan, Modern Methods in Carbohydrate Synthesis ,(1996)
Per J. Garegg, Thioglycosides as glycosyl donors in oligosaccharide synthesis. Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 52, pp. 179- 205 ,(1997) , 10.1016/S0065-2318(08)60091-8
S. A. Mucklejohn, N. W. O'Brien, T. R. Brumleve, High-purity iron(II) iodide: preparation, vapor pressure, and vapor composition, 792 to 1138 K The Journal of Physical Chemistry. ,vol. 89, pp. 2409- 2415 ,(1985) , 10.1021/J100257A051
Eike Bauer, Recent Advances in Iron Catalysis in Organic Synthesis Current Organic Chemistry. ,vol. 12, pp. 1341- 1369 ,(2008) , 10.2174/138527208786241556
Carles Malet, Josep Lluis Viladot, Ana Ochoa, Belen Gallégo, Carme Brosa, Antoni Planas, Synthesis of 4-methylumbelliferyl-β-d-glucan oligosaccharides as specific chromophoric substrates of (1 → 3),(1 → 4)-β-d-glucan 4-glucanohydrolases Carbohydrate Research. ,vol. 274, pp. 285- 301 ,(1995) , 10.1016/0008-6215(95)00102-Y
Saeed A. Abbas, Joseph J. Barlow, Khushi L. Matta, A convenient synthesis of p-nitrophenyl 1-thio-β-d-glycopyranosides by using resin-bound p-nitrobenzenethioxide Carbohydrate Research. ,vol. 100, pp. C33- C34 ,(1982) , 10.1016/S0008-6215(00)81065-4
K. B. Yoon, J. K. Kochi, Ferric iodide as a nonexistent compound Inorganic Chemistry. ,vol. 29, pp. 869- 874 ,(1990) , 10.1021/IC00329A058
Sylvain Gaillard, Jean-Luc Renaud, Iron-catalyzed hydrogenation, hydride transfer, and hydrosilylation: an alternative to precious-metal complexes? Chemsuschem. ,vol. 1, pp. 505- 509 ,(2008) , 10.1002/CSSC.200800071
K. C. Nicolaou, Nicolas Winssinger, Joaquín Pastor, Frederik DeRoose, A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of a Heptasaccharide Phytoalexin Elicitor (HPE) Journal of the American Chemical Society. ,vol. 119, pp. 449- 450 ,(1997) , 10.1021/JA963482G
El Sayed H. El Ashry, George H. Labib, Yeldez El Kilany, Exceptional oxidation, with copper ion, of the bis-[(o-chlorophenyl)hydrazone] of l-threo-2,3-hexodiulosono-1,4-lactone Carbohydrate Research. ,vol. 52, pp. 251- 254 ,(1976) , 10.1016/S0008-6215(00)85970-4